Vacation rentals with a pool in Cherry Garden

Vacation home in Kingston

A modern living area is showcased, featuring a plush gray sectional sofa adorned with yellow accent pillows. A sleek glass coffee table sits in front, and a wall-mounted television is placed above a decorative stone feature. The space boasts an open layout that connects to the kitchen.

4.95 out of 5 average rating, 120 reviews

Elegant 2 bedroom / 2bathroom Apartment w/pool.

Located only 5 minutes away from Half Way Tree & Barbican Center, this newly built apartment offers a unique taste of style and elegance that is sure to cater to your "home away from home needs". This 2 bedroom / 2 bathroom gem, manned by 24-hr security, boasts a décor that is modern and comfortable. It is further complemented by its close proximity to business hubs, including Starbucks, Megamart, Wendy's and the Canadian Embassy. Amenities include gym, pool, free-wifi, cable and rooftop lounge.

4.9 out of 5 average rating, 136 reviews

A spacious living area features a modern sofa with bright accent pillows, paired with a decorative rug. Natural light enters through the balcony doors, which are flanked by sheer curtains. A dining table and wall-mounted TV are visible, enhancing the inviting layout.

Condo in New Kingston

New Kgn condo with gym, 24h security, free parking

Relish the grandeur of this centrally located 1 bedroom New Kingston getaway with serene views of the hills, beautiful decor and modern amenities tailored to your comfort. You will most definitely love the light & airy feel of this condo and its close proximity to all the popular attractions, entertainment spots, restaurants and supermarkets, in Kingston, Jamaica. Send us a message so that we can answer any questions you may have :) P.S. The pool is currently under renovation until Dec 9, 2025

A bright and airy living area features a large sectional sofa and a coffee table, complemented by a flat-screen television mounted on the wall. Sunlight filters through sheer curtains, illuminating the space and offering views of the balcony with outdoor seating.

4.94 out of 5 average rating, 189 reviews

Light &Bright 1-bedroom Apartment w pool

This bright and stylish centrally located 1-bedroom apartment is the perfect space for your stay. It’s Located within 8mins walking distance or 2mins drive to Starbucks, supermarket, pharmacy, and local restaurants. The contemporary living space has everything to make you feel at home Wi-Fi, local cable, Netflix, washer/dryer, ac units, king size bed, a well equipped kitchen and tableware. Have a glass of wine and enjoy the beautiful sunset on the balcony after a long day of work or play.

A cozy living room is highlighted by a large sectional sofa adorned with decorative pillows. A vibrant area rug adds color to the space, while a wall-mounted television and framed artwork enhance the modern decor. A small potted plant brings a touch of greenery.

4.8 out of 5 average rating, 103 reviews

It's an Experience (IAE) Homes JM: Paddington Ter

Life is short & memories should last a lifetime! Welcome to It's An Experience (IAE) Homes where all your needs and desires are within a finger tip's reach. Our modern yet elegant amenties, tasteful architectural pleasing complex, nestled in one of the City's most highly sought tranquil residential area will provide pure bliss during your stay. We are still close to EVERTHING of interest which will allow moving around convenient and accessible. IAE is the therapy the travel doc ordered.

Apartment in Beverly Hills

A modern living area is presented with a black leather sofa adorned with decorative pillows in shades of blue and white. A matching ottoman complements the seating. A glass dining table with black chairs is visible in the background, featuring unique cut-out designs.

4.85 out of 5 average rating, 225 reviews

CityFive Kgn 1 BDRM Blue Mtn & City Views fr Deck

***IMPORTANT*** READ ALL SECTIONS BELOW Recently remodeled, this property affords you a view of the Blue Mountains and parts of Kgn central. It is modern in design and furnishings, located in a quiet neighbourhood and central to most major areas. For the business traveller, wi-fi connection and easy accessibility to the central business district. For families, you can ‘Netflix and Chill’. For the vacationer, 10 mins to Bob Marley Museum or 35 to Port Royal. PLS INQUIRE FOR 5 OR MORE

The living room features a cozy seating area with a blue sofa and two accent chairs. A glass coffee table is positioned in front of the sofa, with a small dining table for two in the corner. Light-colored curtains frame the windows, and a smart TV is mounted on a white console.

4.92 out of 5 average rating, 168 reviews

Cozy 1‑BR w/ Pool • Steps from US Embassy

Location, location, location! This comfortably furnished air-conditioned one bedroom ground floor apartment is in the heart of Liguanea, the golden triangle - 7 minutes walk to the US Embassy, supermarkets, shopping centres, restaurants, and Starbucks, and 5 minutes drive to New Kingston. The unit includes coded keypad entry to the building, 24-hour security, fully equipped kitchen, WiFi, smart TVs, cable, parking, swimming pool, hot water and in-unit laundry (for an additional fee).

A modern living area is presented with a spacious gray sectional sofa adorned with colorful cushions. A coffee table sits centrally on a patterned rug. Large windows with striped blinds provide natural light, complemented by a standing lamp and plants that enhance the inviting atmosphere.

4.87 out of 5 average rating, 121 reviews

Urban Lifestyle @ Mont Charles - Liguanea Kingston

Enjoy the best of the city at a stylish condo located at Liguanea in Kingston. This City getaway is conveniently close to: U.S.-Embassy, Sovereign North plaza, Progressive Shopping Plaza, Sovereign Centre, Bob Marley Museum, Banks, Barbican area, shopping & restaurant locations. With a modern designed interior, the apartment is perfect for families, friends, solo travelers, visiting for business or leisure. Relax at a secure complex, featuring a pool, a roof terrace +more

4.91 out of 5 average rating, 147 reviews

An open-plan living and dining area is highlighted by a modern grey sofa and a stylish circular coffee table. Bright overhead light fixtures add ambience, while a large piece of wall art introduces elegant geometric patterns. A small vase with white flowers adds a touch of greenery.

Apartment in Liguanea

Fab Homes JA . Paddington Terrace

Retreat to our luxurious 1 bed room condo conveniently located in the heart of Kingston 6. Built in 2021, this 6 story condominium is equipped with a top pool for fun and relaxation . You will be in close proximity to Bob Marley Museum, Devon House, National Stadium, supermarkets, TGIF, Starbucks, Half Way Tree, Sovereign Centre, hospitals and all major banks; a maximum of 5 to 15 minutes drive to any of these locations and only 40 minutes from the airport.

4.83 out of 5 average rating, 294 reviews

The modern exterior of the gated complex is displayed, featuring a blend of light and dark blue facades. The entrance sign indicates 'Harloe's Place,' while multiple balconies are visible on the upper floors, enhancing the structure's contemporary design.

Apartment in Kingston

One bedroom, one bathroom Apt Kingston

Simply but elegantly furnished one bedroom apartment in a gated complex on the 3rd floor. It is found within a gated complex with 24 hour security and located close to shopping and and entertainment hubs in Kingston. It features wooden accented furniture tastefully organized for style and comfort. The unit comes with Wifi And Cable television and a fully functional kitchen. Geographically located within walking distance from Devon House and Half Way Tree.

A modern kitchen is presented with sleek cabinetry and stainless-steel appliances. Soft blue lighting highlights the granite countertops. An electric kettle and coffee maker are visible, alongside decorative kitchen mats. A window offers natural light, enhancing the functional space.

4.88 out of 5 average rating, 306 reviews

Stunning smart apt with pool & amazing sunset view

Enjoy a brand new 1 BR 650 sq. feet apartment with all the modern amenities to make your stay effortless, tranquil and relaxing. The space features a master bedroom with en-suite bathroom and scenic balcony views perfect for a late night drink or morning coffee. All rooms are equipped with smart voice controlled AC's. The flat is fully Alexa enabled and gives your the flexibility of using voice commands for all lights, bedroom fan, music etc.

4.9 out of 5 average rating, 134 reviews

A modern living area features a cozy fireplace displayed on a sleek wall-mounted TV. A soft, light-colored sofa with contrasting dark cushions is paired with a stylish black chair. A large potted plant adds a touch of nature, while large windows invite natural light into the space.

Apartment in Kingston

Modern Escape with Rooftop Pool & Sunset Views

Enjoy a stylish experience at this centrally-located place. Parkhurst 103 is situated in a modern newly built apartment complex in the heart of Kingston Jamaica. Easily one of the most central units available. Walking distance from Krispy Kreme , Starbucks, Devon House, and Canadian Embassy. It is a modern contemporary design curated for both comfort and style. Whether business or pleasure Parkhurst 103 isperfect for your stay in Kingston.

Apartment in Constant Spring

A parking area is visible in the foreground, surrounded by multi-story buildings with a tropical landscape in the background. Palm trees add greenery, while a guardhouse stands at the entrance. The sky is partly cloudy, providing a bright and open atmosphere.

4.76 out of 5 average rating, 125 reviews

Kingsley's Hillman Apartment with pool

Sparkingly clean and Comfortable apartment in gated community with security. Ideally located in the safe, quiet and convenient area of Constant Spring just below Manor Park and the ConstantSpring Golf Club. Enjoy a relaxing but fun-filled stay in Kingston Jamaica as the apartment is within close proximity to restaurants, supermarkets, shopping malls and entertainment.

Popular amenities for Cherry Garden rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.63 out of 5 average rating, 16 reviews

A well-maintained exterior view of a single-story house, featuring a lush green lawn and a palm tree. A sprinkler gently waters the grass, while two chairs are positioned on the porch. A car is parked in the driveway, completing the serene setting.

Home in Caymanas Estate

Caymanas lovely home away from home

A bottle of red wine is placed on a table, accompanied by two wine glasses filled with wine. The backdrop features a panoramic view of the city lights shimmering at night, offering a serene and inviting atmosphere for relaxation.

4.96 out of 5 average rating, 27 reviews

City Scape Serenity

4.88 out of 5 average rating, 111 reviews

The exterior of the modern penthouse is shown, featuring a well-maintained garden with tropical flora. The building’s design includes multiple rounded balconies and large windows, allowing for natural light. A clear blue sky serves as a backdrop, enhancing the tranquil atmosphere.

Home in Beverly Hills

Akwaaba Penthouse Luxury Suite

4.91 out of 5 average rating, 46 reviews

A single-story home is set in a spacious yard with well-maintained grass and potted plants. The front porch features a welcoming seating area under an archway. The backdrop includes rolling hills under a clear blue sky, emphasizing the serene surroundings.

Home in Caymanas Estates

Serene Vistas, Caymanas Country Club

A pathway lined with well-maintained greenery leads up to the villa. The steps are flanked by palm trees and lush landscaping, with the villa's exterior visible in the background under a clear blue sky.

4.69 out of 5 average rating, 13 reviews

The Marley's Elite Suite- 4br, 3 bth with Jacuzzi

A paved pathway lined with palm trees leads through a colorful parking area showcasing several vehicles. Multiple two-story buildings with balconies are visible in the background, each featuring a warm color palette that complements the serene surroundings.

5 out of 5 average rating, 3 reviews

Fairview Near AC Hotel Kingston - 2BR

Home in Saint Catherine Parish

A modern home is surrounded by well-maintained landscaping, featuring a manicured lawn and colorful flower beds. A curved pathway of stones leads to the entrance, which is highlighted by a decorative lantern. Nearby palm trees add to the inviting outdoor setting.

4.9 out of 5 average rating, 135 reviews

The Caymanas Villa

The exterior of the property features a modern design with a spacious paved driveway. Potted plants flank the entrance, adding greenery. A clear blue sky complements the structure, while covered parking areas are visible alongside the main building.

5 out of 5 average rating, 51 reviews

Urban Escape

Condo rentals with a pool

A bright living area is furnished with a large sectional sofa and accent chairs, complemented by a contemporary rug. Natural light filters through expansive windows, showcasing a view of the outdoors. A TV console is located beneath a wall-mounted television, enhancing the space's functionality.

4.87 out of 5 average rating, 139 reviews

Airy & modern 2br condo w/pool

4.9 out of 5 average rating, 102 reviews

Modern Condo/Gated/ Pool/ Gym/WIFI/AC/ Hot Water

The rooftop pool area is surrounded by a smooth stone deck with a wooden pergola providing shaded seating. Lush greenery and distant hills are visible in the background, creating a scenic view. The pool’s clear water reflects the blue sky above.

5 out of 5 average rating, 38 reviews

Chic Central Uptown 1 Bed Condo with Skyline Views

5 out of 5 average rating, 18 reviews

A cozy living area features a modern gray sofa facing a mounted television displaying a calming fire. A dining table accompanied by white chairs is positioned nearby, with large windows covered by light gray curtains, allowing natural light to softly illuminate the space.

Condo in Hope Pastures

Sierra Vista @ Mont Charles - Liguanea Kingston 6

4.86 out of 5 average rating, 102 reviews

A light-filled living area features a spacious beige sofa adorned with colorful throw pillows. A glass coffee table rests on a glossy floor. Panoramic views of the city can be seen through the sliding glass door, leading to a furnished balcony with greenery.

Condo in New Kingston

Luxurious & modern in the heart of New Kingston

A modern living area features elegant white marble flooring and a neutral color palette. A flat-screen TV is mounted on the wall, while a coffee table sits in the center. A dining area with wooden chairs and a small table is visible, leading to an open kitchen space.

4.97 out of 5 average rating, 34 reviews

A Place To Return.

A contemporary living space features a plush sofa with decorative pillows, a sleek entertainment unit with a mounted TV, and a modern rug. A small dining area with stylish chairs is visible in the background, along with a round mirror and subtle decorative plants enhancing the ambiance.

4.85 out of 5 average rating, 146 reviews

Skai’s Executive 1 bedroom Suite with Pool

An aerial view captures a modern apartment complex with a rooftop pool surrounded by sun loungers. The building features a sleek design, with large windows and a grassy landscape below. Nearby, a parking area is visible, providing ample space for vehicles.

4.97 out of 5 average rating, 113 reviews

Modern 1 BD condo w/rooftop pool & majestic views

Other vacation rentals with a pool

4.88 out of 5 average rating, 59 reviews

The Eco Cabin is surrounded by lush greenery, featuring a wooden exterior and solar panels on the roof. A partially covered deck with lounging chairs overlooks the chlorine-free pool, seamlessly integrating indoor and outdoor spaces in a serene natural setting.

Cabin in Blue Mountains

Eco Cabin in Portland Private Waterfall & Pool

4.75 out of 5 average rating, 89 reviews

Luxury Kingston Condo| Pool & 24/7 Security| WIFI!

4.93 out of 5 average rating, 40 reviews

A resort-style pool is surrounded by lush greenery and palm trees. Comfortable lounge chairs and umbrellas are positioned around the pool area, creating an inviting space for relaxation. A spacious outdoor setting is visible, enhancing the tranquil atmosphere.

Apartment in Kingston

24/7 Secured 3B/R w/Pool @ Lux Echelon Escape

4.75 out of 5 average rating, 28 reviews

A serene pool area is showcased with clear blue water surrounded by a spacious deck. A gazebo sits nearby, providing shade. The landscape below features a panoramic view of lush greenery and the city, extending under a bright blue sky.

Apartment in Norbrook

Serenity On The Hills of Norbrook Heights.

4.88 out of 5 average rating, 95 reviews

An aerial view of the living area showcases a modern design with large windows allowing natural light. A plush gray sofa is paired with a round coffee table on a blue rug. A flat-screen TV is mounted above a sleek entertainment unit, complemented by decorative plants.

Apartment in Havendale

The wonderlust

4.98 out of 5 average rating, 42 reviews

A private pool is framed by landscaped greenery and palm trees, providing a refreshing space for relaxation. Two lounge chairs are positioned nearby on the sunlit deck. The adjacent house features arched windows, contributing to a serene and inviting outdoor setting.

Villa in Kingston

Lea On The Hill Cheerful with view of the city

5 out of 5 average rating, 33 reviews

A modern living area features two light chairs with brown cushions positioned beside a small side table. A sleek TV is mounted on a dark feature wall, complemented by textured wallpaper. A tall green plant adds a touch of nature to the space.

Apartment in Liguanea

Genesis @ SMT | Modern 1BR Apt | Walk to Sovereign

A modern living area features a navy blue sectional sofa adorned with decorative cushions. A round coffee table sits on a textured rug, positioned beneath a ceiling fan. Light-colored curtains frame a large window, which allows natural light to brighten the space. A small potted plant adds a touch of greenery.